A highly active 4-siloxyproline catalyst for asymmetric synthesis

Advanced Synthesis and Catalysis

Volumn 346, Issue 12, 2004, Pages 1435-1439

  Hayashi, Yujiro ^a   Yamaguchi, Junichiro ^a   Hibino, Kazuhiko ^a   Sumiya, Tatsunobu ^a   Urushima, Tatsuya ^a   Shoji, Mitsuru ^a   Hashizume, Daisuke ^b   Koshino, Hiroyuki ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b RIKEN   (Japan)

Author keywords

Asymmetric synthesis; Mannich reaction; Organic catalysis; Oxidation; Proline

Indexed keywords

CARBONYL DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MANNICH REACTION; MICHAEL ADDITION; SYNTHESIS;

EID: 9144258075     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404166     Document Type: Article

References (73)

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14. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
15. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
16. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
17. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
18. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
19. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
20. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
21. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
22. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
23. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
24. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
25. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
26. For selected studies of proline-catalyzed aldol reaction, see: a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386; b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 123, 5260; c) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 12911; d) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798; e) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620; f) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475; g) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2797; Angew. Chem. Int. Ed. 2003, 42, 2785; h) N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420; i) A. B. Nothrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152; j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839; k) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, Tetrahedron Lett. 2004, 45, 4353.
27. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
28. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
29. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
30. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
31. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
32. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
33. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
34. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
35. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
36. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
37. For selected studies of the Mannich reactions, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; c) A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842; d) A. Cordova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866; e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, III, J. Org. Chem. 2003, 68, 9624; f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301; g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677; h) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208; i) A. Cordova, Chem. Eur. J. 2004, 10, 1987; j) review; see: A. Cordova, Acc. Chem. Res. 2004, 37, 102.
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73. [5 h]